Your fixed costs in airplane ownership are the killer. Most people find that owning their own plane is much much higher than renting from an FBO, or being in a flying club.
Now, if you are going to be flying 200 hours or more a year, ownership starts to look pretty good. At 100 hours/year, you are depending on a planes appreciation to break even. The average private pilot flies around 20-25 hours/year.
The good news, light sport aircraft, where you can get a repairmans certificate to do the annual inspection and maintenance yourself within some categories. Unfortunately, the legislative process is pretty slow, so at this point, the process is still up in the air. However, that just takes care of maintnenance labor, and aircraft parts are spendy. Case in point is an alternator. We could get one at the local autoparts store for $38, but the aviation version was $400. The part numbers were identical with the exception of a one character suffix. In a nutshell, the difference was the aviation version had a yellow tag, was PMA approved, and had a paper trail. Mechanically and electrically it was identical.
Back when I was a college student, I was a mechanics assistant, and by the time I graduated, I could have picked up my mechanics certificate, but was too foolish to do so. Otoh, the experience gained on hundreds of annual inspections, as well as repair and replace was incredible.
I've worked for a couple FBO's since then as a flight instructor, and all too often run into folks purchasing an aircraft and then running into severe financial difficulties, thus limiting their ability to stay current.
As far as IFR goes, what the regs say, and really being safe are 2 different things. To be safe, you really need around 50 hours of IFR a year, and if you want to fly approaches to minimums, figure on 100-200 hours of IFR, apart from VFR time. Otoh, I know lots of guys that maintain currency with 12 hours of IFR/year, but I would not want to fly approaches in actual conditions with them. Fortunately, most people in this situation, just use their rating to fly enroute, and break out into VFR conditions.
As far as blood pressure goes, as long as meds aren't required, its usually not a big issue. Otoh, if they are, and a special issuance medical is needed, it ends up being a pretty long drawn out affair, with a fair amount of hoop jumping. Its quite possible, but its not all that easy. Here is a link for some more info
http://www.aviationmedicine.com/bp.htm
Ron